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6 Best Things to Do in Portland, Maine: Everything You Need To Know for Your Trip

These days, road trip season is coming to a close and soon the leaves will start to change…Aaannnddd this is precisely why it’s time to take the best East Coast road trip to Portland, Maine. Apparently, Portland boasts some of the best fall colors in the country. Although, summer here isn’t so bad either. Our two days in Portland, Maine this past August were 75 degrees, sunny, and breezy. This weather only boosted vibes as we strolled the charming brick streets and explored some of the best things to do in Portland, Maine. 

Is Portland, Maine Worth Visiting? 

Short answer…YES. Long answer…My friend and I absolutely loved it here for several reasons. It has the perfect balance of East Coast charm with brick streets, lobster rolls everywhere, lighthouses, and a blueberry growing season. While also remaining young and vibrant with a nightlife scene and trendy spots you might expect to find in a larger city. Next, we loved how easy everything seemed to be. Whether that came from our minimalist, easy-going attitudes that surface as soon as we get together or the city itself I’m not quite sure. But I’m banking on both. I’m not going to lie to you and say we never waited for a table, but when we did, it never seemed long and there was loads of entertainment nearby. Having a car made it easy to explore other parts of the peninsula, so again I’d recommend road-tripping (or renting). Anyway, we didn’t have our days planned out here. We were able to wake up, decide on the fly, and change plans too without any drama. My kind of vacation. 

Where to Stay in Portland Maine

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Here’s the deal, Portland Maine lodging is expensive. At least in our experience. I recommend staying a bit outside of downtown Portland to avoid an overly-priced stay. As I touched on earlier, the city is very accessible by car so this shouldn’t limit your ability to experience the best things to do in Portland, Maine. We stayed in a rustic Airbnb about 10 minutes north of the city. If I had to do it again, I would find a stay in South Portland, go South along historic Route 1, or stay during the week and skip the weekend. There are also more reasonable stays near the airport. If you’re feeling adventurous and can spend more time than two days in Portland, Maine, there is camping and other stays on the Islands in Casco Bay. It’d take a bit more work but I bet it’s beautiful. 

Best Places to Eat in Portland Maine

One of the best things to do in Portland, Maine is eat Lobster. There are lobster rolls everywhere. From the convenience store on the corner to the high-end restaurants specializing in seafood. Of course, we had lobster rolls for both dinners during our stay, however, each one was very different and amazing in its own right. 

Eventide Oyster Co.

On our first night in town, we made the ultimate decision to go to Eventide. A beachy and boutique joint that has incredible oysters, crisp white wine, and of course a gorgeous lobster roll. I’m not very well-versed in seafood, so the waiter chose oysters for us and I ordered the classic lobster roll. It was the perfect introduction to Maine. If there is anything I can recommend for Eventide, it’s to get a reservation or get there early to reserve your spot. Our wait was over an hour for two people. All good though, we went next door to The Honey Paw for some Asian-inspired snacks and more wine while we waited. 

The Highroller Lobster Co.

Our second lobster roll was just around the corner and up the block at Highroller Lobster Co. We like to call Highroller the “fast-foodier” option for lobster in Portland, Maine. There’s a vibrant energy inside and the menu goes beyond the classics. At Highroller, you can find lobster tacos, lobster grilled cheese, lobster mac, and yes a surf and turf burger. We ate an early dinner here and didn’t need another meal for the rest of the night. Go to The Highroller if you’re really feeling hungry.

Rose Foods

Our favorite breakfast on the trip was at Rose Foods where New York-style bagels are made fresh in-house every morning. Starting with a beautiful base is essential, but Rose Foods takes it to the next level with deli bagel sandwiches featuring lox, whitefish salad, pastrami you name it. We went with the classic Nova Lox on an everything bagel and indulged in the free refills of diner coffee while we read the NY Times. Just two old ladies and an authentic deli experience.

Best Things to do in Portland, Maine

Besides incredible food, Portland offers tourist attractions, shopping, and stuff for the outdoorsy folk too. One thing you should not compromise on is seeing a lighthouse while you’re in Portland. In fact, you kind of can’t miss them. They’re all over town and exceeded our expectations. There are also several adorable pockets of the city to stroll the brick streets and see where they take you. Of course, your journey can’t end without spending some time relaxing on an East Coast Beach. 

Portland Head Light

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Okay, I can’t lie when I tell you that this is definitely a tourist attraction. But goodness it is worth it. I recommend walking along the path that lines the coast to get as many different angles and views of the lighthouse as you can. Also, the lighthouse is located in Fort Williams Park which is absolutely gorgeous. Definitely budget some time to hang out here and have a picnic or grab a snack from the food trucks. Yes, of course, there is a food truck serving up more lobster.

Crescent Beach State Park

Okay, I can’t lie when I tell you that I got this rec. from Noah Kahan. If you have no idea what I’m referencing go listen to his song Maine…Anyway, we spent the most perfect afternoon on Crescent Beach looking for sea glass, wading in the waves, and relaxing in the sand. For even more entertainment, you can rent kayaks and paddleboards here. Our favorite part of the beach, however, was the L.L. Bean Beach Box which offers free beach items like umbrellas, beach toys, and chairs free of charge. Just use the items and return them when you’re done. It costs $8 per person for non-Maine residents to enter the park, and $6 if you’re a Maine resident.

Old Port Shopping & Nightlife

Old Port is a historic part of downtown Portland, Maine that offers cobblestone streets and views of the Portland Harbor while you peruse souvenir shopping and clothing boutiques. I found awesome, unique gifts along Commercial Street in Old Port. When the sun begins to set, however, Old Port is a great spot to find a cocktail or pint. I recommend starting your night with excellent views and delicious cocktails at Luna Rooftop. We ended our night at The Porthole, a dockside pub with live music and a disco ball. Lots of bachelor parties here if that gives you any idea of the vibe…still, very fun.

Maine Beer Company

Just a short drive from Portland to Freeport, Maine, you’ll find Maine Beer Company. Honestly stepping into this place feels a bit like stepping into an eco-friendly spa. Maybe it’s the water fountain in the middle of the tasting room, or maybe it’s that you leave feeling extra good about drinking beer. Maine Beer Co. is different because it is committed to the environment. Whether that’s donating 1% of profits to environmental nonprofits or their use of clean energy and sustainable waste practices.

Explore the Eastern Promenade Portland, Maine

One of the best things to do in Portland, Maine apparently is to peruse the Eastern Promenade. I say apparently because we ran out of time and didn’t make it here, unfortunately. The Eastern Promenade is Portland’s largest park and offers views of Casco Bay, walking trails, several historic memorials, a beach, and boat launches. Sunrise and sunset are supposedly top-notch from the park and you can often find food trucks to satiate any cravings.

After my visit here, I consider Portland, Maine one of the Best East Coast road trip destinations. Along with the immaculate scenery, there is a potent history and East Coast vibe that makes you feel immersed in the culture of the city. It’s safe for solo travel, and fun for bachelor parties while remaining great for families too. Overall, the best things to do in Portland, Maine are endless and made for everyone. A definite stop on your next East Coast road trip.

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